Triethylamine → methyl 3-isocyanatopropanoate

HRID 1660104Notes

Reaction equation

HRID 1660104 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3]C([O-])=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C>C1(C)C=CC=CC=1>[CH3:9][O:8][C:1]([CH2:2][CH2:3][N:29]=[C:32]=[O:17])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6930703Mono-Methyl Succinate

Product 1

HCID 2769480methyl 3-isocyanatopropanoateYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 600 ml of dry toluene was dissolved 26.4 g of monomethyl succinate, followed by the addition of 55 g of diphenylphosphorylazide and 22 g of triethylamine. The mixture was allowed to stand at room temperature with stirring for 3 hours, after which it was washed with water and dried. The solvent was concentrated to about one-third of its original volume and, finally, the mixture was refluxed for 2 hours. After the solvent was completely evaporated off, the residue was distilled under reduced pressure. By the above procedure there was obtained 13.6 g of the above-indicated compound. b.p.8 : 64°-66° C.

Workup

  1. customto stand at room temperature
  2. washafter which it was washed with water
  3. customdried
  4. concentrationThe solvent was concentrated to about one-third of its original volume
  5. temperaturefinally, the mixture was refluxed for 2 hours
  6. customAfter the solvent was completely evaporated off
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-544cdcbeac7e40dca61b9bdab3597fe2
Source dataset
uspto-grants-1981_12
Patent number
US04307016

Reaction notes

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